The Date
by SomedayonBroadway
Summary: Jack's been sneaking out at night and the boys think it's about time he knock it off


**Hi guys. This was a request from Fanz4life! It was a fun thing to write, very fluffy and out of my comfort zone a little but it was fun to write! I hope you all like it!**

 **Enjoy!**

"Jack...? Where are you goin'?"

The groan that Jack so desperately wanted to let out had to be bitten back. He'd been so sure that he'd make it out that time. After tucking all the littles in bed and making sure all the older boys were sleeping he was sure he'd have tonight to do this. But he couldn't very well tell little Romeo that.

"I'm just goin' fer some fresh air, kiddo..." Jack explained, climbing back through the window and sighing as he picked the somewhat warm eight year old up in his arms so he could carry him back to his bunk. He tried to ignore the way the kid sniffled. It was probably nothing.

He gently lay the boy back down and smiled at him as Romeo tugged some of the blanket off of Racetrack, his bunkmate, who stirred and rolled over to wrapped the child up in his arms. Jack laughed at his friend's protectiveness before leaning down to kiss the crown of Romeo's head. "Get some sleep, pal. Don't worry about me..."

"But 's too cold fer the roof, Jackie..." Romeo yawned as he curled into Race's chest, rubbing at his eyes. At that, the leader of the Lodge let himself chuckle as he shook his head.

" _Goodnight_ , Romeo..." he whispered as the boy began drifting off.

"Don't worry 'bout, cowboy," Race muttered before the older boy could slip away. "He'll just be with his Ace for… what is it Jackie?" the blond boy asked. "Fourth time this week?" he finished smugly, fully prepared for Jack to take off his cap and lightly smack him with it across his shoulder. "Hey!" he argued playfully, hugging his baby brother closer to his chest. The boy seemed to be already back asleep. "I have a harmless child in my arms!" he scolded.

Jack snorted just in time for another voice to speak up from above the trio. "Yeah, harmless," Crutchie chuckled, leaving over the edge of the bunk so he hung upside down as he spoke to his friends. "That's what I call the kid what stole Morris Delancey's wallet, took the cash outta it, n' then put it back _without_ him noticin'," he smirked down at them. Jack chuckled and shook his head.

"Go ta sleep will ya?" he whined, a smile still on his face as he desperately wanted to slip out again but couldn't do long as he had his boys awake and watching him.

But both of them just looked at him with smirks. "So how many times does that make it this week, Jackie?" Crutchie grinned. Jack just rolled his eyes.

"That's strictly 'need to know,'" he replied finally, ready to be able to walk away. "And you, my friends, _don't_ gotta know!" he whispered harshly, pointing at the both of them. They just snickered at him and he shook his head, unable to keep the small smile off of his face. "Just let me be," he sighed, finally. "I'll be back soon." He didn't wait to say goodbye, just rushed out into the night, sneaking through the streets before anyone could object.

"Ya think he'll stick with this one?" Race whispered, Crutchie still hung over the bed, deep in thought.

The younger boy only shrugged. "Anythin's possible, Race…"

Though, neither of them seemed too convinced.

* * *

Katherine was unable to keep the grin off of her face when she heard the pebbles begin to tap at her window. The clock had been ticking on, taunting her for far too long as she forced herself to focus on the mess of papers in front of her. The stories had take control of her and she let them, thankful for some kind of distraction while she waited, but ultimately the boy standing outside her window had consumed her thoughts for much too long.

Rushing over to the window, she laughed at herself as she tripped over her own feet. But when she got to the window and shoved it open, all seemed to be worth it when she saw that stupid, arrogant smirk on her boy's face. But she wasn't about to let him off even, so despite the grin on her face she leaned over and out her window with her arms crossed. "You're late!" she accused playfully, but Jack just laughed.

"I'm here, ain't I?" he laughed back, an innocent and excited look on his face as she shook her head and rushed back through her room so she could sneak out her own front door. She quietly crept out of her room and down the stairs. Immediately when she opened the door she was grabbed from behind just around her waist and picked up. She squealed in surprise and a light laugh met her. "Shhh! You's tryin' ta get your fatha' out here ta send me away?" Jack chuckled turning her around and letting her stand again. She just laughed and pointed at his chest, pushing him backwards a bit.

"Oh-ho, so it's all my fault, then," she laughed as she gripped his shoulders and pushed him up against the wall of her home. Before he could say anything, they both melted into a hungry kiss and Katherine tangled her hands in his hair as he cupped her neck and gripped her around the waist.

Her lips against his was like magic. She was unlike any other girl he'd ever been with. She was smart as hell, she never took no for an answer and she was just as stubborn as he was. They were the perfect match. Though, not everyone seemed to think so.

As she climbed up on him, wrapping her legs around his waist as things got more and more heated, they both failed to notice a man standing just inside the window, glaring hard at them as they continued in their ways. It was a long while before the man decided to clear his throat and make his presence known.

Jack gasped as Katherine jumped away from him. He wiped the grin off of his face as quickly as he could as his hands began to shake a bit.

"Mr. Kelly…" a harsh voice greeted him. The two kids refused to make eye contact when they knew who was watching. Katherine shyly ring her hands behind her back and Jack scratched the back of his head. Neither of them dared speak. "It would be wise if you to go back to your home now and leave my daughter alone at this ungodly hour."

 _Damn_ , Jack thought finally looking up the woman standing next to him, giving her a sad smile as she looked at him a bit helplessly. "Sorry, Mr. Pulitzer… I'll see ya tomorrow…" he muttered before giving his girl a quick kiss on the cheek and dejectedly rushing off.

Katherine sighed as she watched Jack walk off, hands in his pockets until he grabbed the cap off of his head and rung it around in his hands. It was quite obvious he was just about as upset as she felt. This was the fourth time this had happened in the past week. It was always something different. Her father, her father's assistant, a lead on a story, one of the boys needing Jack back at the house. So the woman held back a groan when she turned to meet the most powerful man in New York City.

"He's a charming young man, darling," he started off, fixating his robe tighter around himself as he spoke. The comment surprised Katherine, but she didn't speak, waiting for- "He's a distraction." There it is, she thought bitterly as she shook her head, turning to go back to her room without a word, but the old man grabbed her arm gently and turned her around. "You have a great career and a wonderful future in front of you, sweetheart. Boys are going to become men and you need one that can take care of you."

It was odd for many people to think of old Joseph Pulitzer as a concerned parent. Yet, there he was, standing there trying to convey to his daughter that he just wanted her to have a good future and a good man to protect her. What he didn't know was, that was exactly what she had.

The girl pulled her arm from his grip and gave him a small smile before slipping back inside. Pulitzer nodded in approval, but before he followed her, he caught sight of the boy he'd fought with day in and day out. He ignored the ache that grew in his chest when he could see young Jack Kelly throwing rocks at the ground, irritated at the world. With one final sigh, the man just walked into his home, trying to forget about the boy who had stolen his daughter's heart.

* * *

Jack groaned and let his head fall into his hands. The couch on the ground floor was the only place he could actually wallow in self pity. It was completely silent besides his own irritated mumbles and mutters. That is, until it wasn't.

" _Whoa_ , Jackie…" a quiet voice muttered from the bottom of the stairs. Jack didn't have to lift his head up to see Race giving him an odd look, clearly not understanding what had happened. "How bad is your girl this time?"

The boy in question would admit to complaining about girls since forever. There was always something to be annoyed over. They always wanted gifts, more time, dates, extra kisses. Some of them would even go so far as to tell him to leave his boys so they could have more time and he'd be more focused on her. So he'd walked away, running home to complain to his brothers about how awful these girls were.

Not this time. This time was different. _Ace_ was different.

"'s not my girl, 's-" Jack was cut off by a harsh coughing noise that made his heart skip a beat in surprise. His head shot up towards the noise where he saw three boys were standing. Well, two boys. The littlest of them being cradled in Racetracks arms as he shivered and sneezed. "Oh don't tell me…" the Manhattan leader sighed, shaking his head before standing to his feet and rushing over to little Romeo who was clinging to Race's shirt.

"He's fine, Jack," Crutchie assured, a small smile on his face. "He's just got a little cold. Needed some wata'," he explained as Jack took the little boy into his arms and cradled him to his chest.

"It's gettin' ta be that time a' year, Cowboy…" his second began, solemnly. "Boys're gonna start gettin' sick… and we're gonna need you here…" he tried, watching Jack as he carried their youngest newsie to the kitchen.

"What're ya tryin' ta say, Racer?" Jack asked, letting the little boy sit on the counter while he searched around for a cup before filing it up with some water.

"He's tryin' ta say maybe it's time to move on from this girl. We's need ya here…" Crutchie finished for his friend, limping into the room so he could see Jack better. When he got a look of his brother he could see this… _look_ in his eyes as he rested his hands on either side of little Romeo and shook his head slightly.

"Ya don't undastand…" Jack muttered, watching Romeo slowly sip at the liquid he'd been given. But before he could explain, his brothers were speaking.

"Cmon, Jack," Race deadpanned, resisting the urge to roll his eyes. "Ya do this all the time. Ya get your head fixed on some girl ya hardly know, ya go on a few dates, then it's on to the next…" he explained gently, not wanting to anger the older boy in anyway, simply trying to convey their concerns and reasoning for thinking this would happen. But Jack just scoffed.

He hated this. He truly did. Caring, that is. Sometimes he wondered if guys without hearts had it easier. Maybe Snyder actually got sleep at night and took care of himself. Maybe Pulitzer could pay for a proper meal everyday. Not Jack. Because Jack had a heart and he loved people and cared for people. He protected his boys. And now, someone was coming and and stealing his heart. Though, he wasn't putting up much of a fight.

"There's just one problem with all that, pal…" he sighed, turning to face the two boys who stood in the doorway. "She ain't just some girl… she's…" Beautiful, smart, funny, driven, stubborn, perfect… "She's _Ace_ …" he finally decided, giving a small shrug of the shoulders.

For a moment, all three boys stood around in a bit of a shock. That is, until a sly grin began to spread on Crutchie's innocent face. "No way…" he breathed, elbowing Race who still didn't seem to understand. Jack never named his girls. "You're fallin' for an heiress?" he teased, taking a few steps forward and punching Jack in the arm.

The older boy swatted him away. "So what if is?" he laughed, finally coming to terms with it. He was most definitely falling for an heiress. But not just any heiress; a Pulitzer.

 _Damn_.

"Jack Kelly blushin'..." Race smirked, crossing his arms over his chest. "Neva' thought I'd see the day…" he teased ducking out of the way when Jack took his cap and swung at him. The Italian boy just laughed before walking over to pick up Romeo again. "Well, what're ya gonna do?"

Dumbfounded, Jack stood, waiting for some kind of explanation. He got none. "What?" he asked, confused.

"He means a _date_ , Jack," Crutchie laughed, rolling his eyes. "What're ya gonna do ta show her ya care?"

 _A date._ What the hell was he supposed to do for that? He never took girls out on dates. Normally they just let him sneak in through their windows and that would be that. But this? _Ace_? This was something he'd never experienced before. And for the first time he wanted to do something special. Be something special. So he simply shrugged his shoulders. "I… I dunno…" he muttered.

"Oh Jackie…" Race shook his head and laughed, still cradling an exhausted child to his chest. "We's got some work ta do…"

* * *

If there was one thing Katherine Pulitzer hadn't been expecting to see on her doorstep at five in the afternoon on a Friday night, it was the boy her father constantly chased away wearing what looked to be newly cleaned clothes along with his ever present newsie cap with a single rose in his hand and a charming smirk on his face.

"Jack?!" she squealed in surprise, not quite sure weather to be scared or delighted at the gesture. On one hand, her father would most certainly throw a fit if he saw this just outside his front door, but on the other, the boy she was quickly falling for had left work early to come to her just to see her. "What are you doing here?!" The whisper came out all too happy and Jack laughed.

"I know that you're workin' on a big story right now, and that I's should just let ya work until your fingers go numb, but I…" Jack shook his head, unable to keep the smile off of his face. "I was wonderin' if you's could just take one night off from reportin' ta see a show with me?"

"Jack Kelly…" Katherine giggled, stepping outside to meet her boy and gratefully take the rose he'd picked just for her. "Are you asking me out on a date?" The girl narrowed her eyes, though a grin was all too well seen on her beautiful features.

"Maybe I am…" Jack replied, scratching the back of his neck nervously. "Are you saying yes?"

Without any warning, Jack's arms were full of a fiery brunette and his lips were captured in her's. He grinned into the kiss until she pulled away and he was able to smugly say, "So that _is_ a yes…" he chuckled.

With a sparkly laugh, his girl nodded. So he extended his arm to her and she took it with a smile. "Lead the way, Mr. Kelly…"

And off they went.

* * *

"That's was beautiful…" Katherine breathed as she linked her arm through Jack's and they began aimlessly walking through Manhattan under the moon and the stars.

The boy beside her laughed and nodded in agreement. "Medda always knows how ta surprise ya, even if ya have seen her shows before," he decided, stealing a quick glance down at the woman next to him.

"Those backdrops… where they yours?" Katherine asked, somewhat hesitantly. Jack had always been protective of his work. The offer her father had made him was still standing, but they have him until he was eighteen to decide weather or not he'd take it. He still never liked showing anyone what he did draw.

With a slight nod, Jack responded. "Yeah… yeah I painted some a' them…"

"You have real talent, Jack," she smiled, bumping him a bit as they walked. "Ever thought about leaving to go to art school? Not many others can do things like that," she said seriously. Not that she wanted him to leave, but she wanted him to have a good future.

A snort escaped Jack as he shook his head. "Ain't no way I could leave. Not now…" he admitted, looking down at the ground. "Got too many things here that I love…"

Katherine fought hard to keep the grin off of her face. "Like what?" she inquired curiously, pulling the boy a bit closer to her and reaching for his hand rather than his arm.

"My brothers," he started with a smile, trying not to get all sappy when he thought about the boys who'd gone through thick and thin with each other. "Don't know what I'd do without them…" he sighed with a shrug. "Medda… she's the only motha' I's eva' known…" he stated, clearing his throat to keep away the emotions that threatened him. "There's my penthouse… my sellin' spot…"

He was stalling. He knew that. But when he looked down and saw the fading smile on her face he knew he just needed to say it. " _You_ …" he finally admitted shyly as he stopped walking to just admire how impossibly beautiful she was when her eyes lit up and her mouth hung open in shock.

"Jack…" she breathed, ecstatic tears coming to her eyes. "I-"

"I love you, and it's terrifying and I don't care…" he laughed, taking her hands in his. "I love you, Katherine Pulitzer and I sneak out at night because I can't get you out of my head and I just want to be with you all the time, and the boys don't understand that yet but I just can't stand bein' away from you…"

He didn't know he had so many words in him. But before he could even try and maybe look like the he the tough street kid who'd lead a strike against the most powerful men in the world, she was on him, her lips of his and her hands in his hair, though this kiss was slightly different from the rest. It was still hungry and excited, but something about it was… gentle… something about it was new.

Pulling away from her man, Katherine wiped at her happy tears. "I love you too, Jack…" she whispered. "I always will."

"For sure?"

" _For sure_ ," Katherine teased, mocking his accent before taking his hand in hers and holding it tight. She didn't stop him from bending down for another peck before they continued their walk through the darkened park, all worries and cares behind them.

They were two kids in love. And nothing in the world could change that.

 **There it was. Again, fluff really isn't my thing. Here was the request ;)**

 **"I have this idea in my head that once Jack and Kath really start to take their relationship seriously that they can't find time to be with each other. So Jack's always with the boys cuz the boys all complain about how much time he spends with Kath. And Kath is REALLY starting to become real reporter. So, eventualy after some EXTREME thirst Jack tells the boys how much she means to him he's like "she's not just some girl" or whatever and it's super sweet. Then Kath and him like go to Medda's 4 a show then 2 Tibby's or Jacobi's and then they go 4 a romantic moonlit walk in Central Park and he tells her he loves her"**

 **I feel like you probably wanted the boys a little madder at Jack, but I did my best. I hope you liked it!**

 **Thank you so much Fanz4life! I can't wait to write all of your other requests too!**

 **As always, thanks for reading! Make sure to tell me what you liked, what you didn't, what you'd change or what you'd improve by leaving me a review! Love ya, fansies!**


End file.
